The transition to adulthood is an underresearched topic for cross-systems youth, defined as young people who have experienced homelessness, child welfare system involvement, and educational challenges. This qualitative study explored processes of resilience in the transition to adulthood for cross-systems youth aged 18 to 24 (n = 20). Analysis of in-depth interviews using a grounded theory open coding process revealed two thematic concepts, striving and dreaming. As illustrated in two case studies, striving was characterized by participants having specific educational and career goals and making strategic choices about programs and resources. In contrast, the dreaming concept indicated participants having little understanding of the steps and resources needed to achieve their goals. Implications for practice include the importance of helping cross-systems youth maintain supportive relationships with families of origin and peers to enhance striving, and the use of motivational interviewing to assist emerging adults in gauging their readiness and motivation to set and pursue goals.